I believe you should. Apple locks down their devices, so you cannot customize them at all. Jailbreaking allows you to get root access to your device; in other words, jailbreaking allows you to do ANYTHING you want to your device. You can tweak out your device to add functionality, you can theme your Springboard, and, if you're into pirating, you can get apps for free using Installous.
People may occasionally mess up their iDevices, but the worst thing you can do can be fixed by just restoring it. Also, jailbreaking may void the warranty, but you can restore it and they will never know you jailbroke it. I took my jailbroken iPhone 4 to the Apple Store because the battery was acting up. The phone was previously jailbroken, so I restored it and took it in. They replaced the phone with no questions asked.
I hope this helps!